Methanol → HCID 10070049, compound

HRID 1784159Notes

Reaction equation

HRID 1784159 reaction equation
[C:1]1([S:7]([C:10]2[C@H:17]3[C@H:15]([O:16]3)[C@H:14]([CH3:18])[C@H:13]([OH:19])[C@@H:12]([CH3:20])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.[Si:29](OS(C(F)(F)F)(=O)=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].CO>C(Cl)Cl>[C:1]1([S:7]([C:10]2[C@H:17]3[C@H:15]([O:16]3)[C@H:14]([CH3:18])[C@H:13]([O:19][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@@H:12]([CH3:20])[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 10379699HCID 10379699, compound

Product 1

HCID 10070049HCID 10070049, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of alcohol α36 (62 mg, 0.21 mmol) and 2,6-lutidine (50 μL, 0.43 mmol) in CH2Cl2 (2 mL) was cooled to −78° C., and 63 μL (0.27 mmol) of TBSOTf was added. The stirred cold solution was warmed to 0° C. over 5 h. MeOH (40 μL, 1 mmol) was then added to quench the excess TBSOTf. The resulting mixture was concentrated via rotary evaporation, and the crude residue was purified by flash column chromatography (EtOAc/hexanes; 1:5) to afford 82 mg (95%) of α37 as a white solid. mp 89.0-90.0° C.; [α]20D=−30.5 (c=0.61, CH2Cl2); 1H NMR (CDCl3, 300 MHz) δ 7.93-7.97 (m, 2H), 7.55-7.70 (m, 3H), 7.09 (d, J=5.1 Hz, 1H), 3.70 (dd, J=8.4 Hz, 2.1 Hz, 1H), 3.67 (d, J=4.8 Hz, 1H), 3.37 (dd, J=7.2 Hz, 4.2 Hz, 1H), 2.60 (m, 1H), 2.49 (m, 1H), 1.26 (d, J=7.2 Hz, 3H), 0.90 (s, 9H), 0.74 (d, J=7.2 Hz, 3H), 0.10 (s, 3H), 0.09 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 146.0, 140.2, 136.1, 133.7, 129.3, 128.4, 74.5, 56.8, 48.7, 40.9, 36.9, 25.9, 18.4, 18.1, 9.7, −4.3, −4.4; Analytical. Calculated for C21H32O4S: C, 61.72; H, 7.89. Found: C, 61.39; H, 7.59.

Workup

  1. temperatureThe stirred cold solution was warmed to 0° C. over 5 h
  2. customto quench the excess TBSOTf
  3. concentrationThe resulting mixture was concentrated via rotary evaporation
  4. customthe crude residue was purified by flash column chromatography (EtOAc/hexanes; 1:5)

Sources & evidence

ORD record
ord-7062d2f0602944bcae3a395bd632b80a
Source dataset
uspto-grants-2009_03
Patent number
US07501535B2

Reaction notes

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